Showing metabocard for N-Acetylvaline (MMDBc0000460)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:16 UTC
Update Date2024-04-30 19:32:29 UTC
Metabolite IDMMDBc0000460
Metabolite Identification
Common NameN-Acetylvaline
DescriptionN-Acetyl-L-valine or N-Acetylvaline, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylvaline can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylvaline is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-valine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylvaline can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free valine can also occur. Excessive amounts N-acetyl amino acids including N-acetylvaline(as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylglutamine, N-acetylisoleucine, and N-acetylthreonine) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylthreonine, are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb488d5e20>


  Mrv1652303062020242D          

 11 10  0  0  0  0            999 V2000
 9987.2189 9987.6461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.2189 9986.8221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9986.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6482 9986.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9985.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.5034 9988.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.7889 9987.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.5034 9988.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9988.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6482 9987.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9988.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fdb488d5e20>

HMDB0011757
     RDKit          3D
N-Acetylvaline
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.2710   -0.8844    0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.0946    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594    0.5194    1.7055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9244   -0.0554   -0.1971 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    0.6177    0.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3659    1.9841   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2526    2.4793   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    2.9896    0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626   -0.3139   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -1.6892    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    0.1899   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760   -1.9810    0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -0.7048   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1635   -0.7769    0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.5117   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173    0.5984    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892    3.5816   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.5394   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -1.6429    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2829   -2.0923    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4235   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -0.7264   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550    0.8342   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803    0.6424    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  1
  8 17  1  0
  9 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 11 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fdb488d5e20>


  Mrv1652303062020242D          

 11 10  0  0  0  0            999 V2000
 9987.2189 9987.6461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.2189 9986.8221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9986.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6482 9986.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9985.5836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.5034 9988.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.7889 9987.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.5034 9988.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9988.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6482 9987.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9345 9988.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000460

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)[C@H](NC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

> <INCHI_KEY>
IHYJTAOFMMMOPX-LURJTMIESA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.185

> <EXACT_MASS>
159.089543283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.274910030459353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamido-3-methylbutanoic acid

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
0.12763050966666675

> <ALOGPS_LOGS>
-0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.493791320219575

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.112961676275345

> <JCHEM_PKA_STRONGEST_BASIC>
-1.633990390486503

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
38.9367

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-valine, N-acetyl-

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb488d5e20>

HMDB0011757
     RDKit          3D
N-Acetylvaline
 24 23  0  0  0  0  0  0  0  0999 V2000
   -3.2710   -0.8844    0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.0946    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594    0.5194    1.7055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9244   -0.0554   -0.1971 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    0.6177    0.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3659    1.9841   -0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2526    2.4793   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348    2.9896    0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626   -0.3139   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -1.6892    0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    0.1899   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760   -1.9810    0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5199   -0.7048   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1635   -0.7769    0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -0.5117   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173    0.5984    1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892    3.5816   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.5394   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -1.6429    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2829   -2.0923    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -2.4235   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -0.7264   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7550    0.8342   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803    0.6424    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  1
  8 17  1  0
  9 18  1  0
 10 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
 11 23  1  0
 11 24  1  0
M  END
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PDB for #<Metabolite:0x00007fdb488d5e20>

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8642.8098643.606   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8642.8098642.068   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8644.1448641.296   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8645.4778642.068   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8644.1448639.756   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8641.4738644.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8640.1398643.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8641.4738645.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8644.1448644.376   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8645.4778643.606   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8644.1448645.916   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007fdb488d5e20>

COMPND    HMDB0011757
HETATM    1  C1  UNL     1      -3.271  -0.884   0.150  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.102  -0.095   0.605  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.159   0.519   1.706  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.924  -0.055  -0.197  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.286   0.618   0.291  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.366   1.984  -0.095  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.253   2.479  -0.902  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.535   2.990   0.377  1.00  0.00           O  
HETATM    9  C5  UNL     1       1.363  -0.314  -0.216  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.270  -1.689   0.416  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.727   0.190  -0.425  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.976  -1.981   0.279  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.520  -0.705  -0.925  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.164  -0.777   0.811  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.934  -0.512  -1.109  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.217   0.598   1.414  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.989   3.582  -0.283  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.012  -0.539  -1.336  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.702  -1.643   1.407  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.283  -2.092   0.639  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.739  -2.423  -0.243  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.322  -0.726  -0.811  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.755   0.834  -1.356  1.00  0.00           H  
HETATM   24  H13 UNL     1       3.280   0.642   0.374  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6    9   16
CONECT    6    7    7    8
CONECT    8   17
CONECT    9   10   11   18
CONECT   10   19   20   21
CONECT   11   22   23   24
END
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SMILES for #<Metabolite:0x00007fdb488d5e20>

CC(C)[C@H](NC(C)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fdb488d5e20>

InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1
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Synonyms
ValueSource
(2S)-2-Acetamido-3-methylbutanoic acidChEBI
(2S)-2-Acetamido-3-methylbutanoateGenerator
N-Acetylvaline, (L)-isomerHMDB
N-Acetyl-DL-valineHMDB
N-Acetylvaline, (D)-isomerHMDB
Acetyl-valHMDB
N-Acetyl-D,L-valineHMDB
(S)-2-Acetamido-3-methylbutanoic acidHMDB
2-Acetamido-3-methylbutanoic acidHMDB
AcetylvalineHMDB
L-N-AcetylvalineHMDB
N-Acetyl-L-valineHMDB
N-AcetylvalineChEBI
Molecular FormulaC7H13NO3
Average Mass159.185
Monoisotopic Mass159.089543283
IUPAC Name(2S)-2-acetamido-3-methylbutanoic acid
Traditional NameL-valine, N-acetyl-
CAS Registry NumberNot Available
SMILES
CC(C)[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1
InChI KeyIHYJTAOFMMMOPX-LURJTMIESA-N